15,709

Caroline County, MD Homes

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  • /9

    $225,000 Sold Jun 11, 2025

    19 S 8th St, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1981

    Last Sold Summary

    • $260/SF
    • 9 Days On Market

    Current Estimated Value $235,802

    Last Listing Agent Myisha Walker Long & Foster Real Estate, Inc.

    19 S 8th St, Denton, MD 21629
    • /39

      Est $438,029 Not Listed For Sale

      21303 Dover Bridge Rd, Preston, MD 21655

      • 3 Beds
      • 3 Baths
      • 2,607 Sq Ft
      • Built 1998
      21303 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 25% Above List Price
      • $134/SF
      • 16 Days On Market
      • Last Sold Price $350,000
      • Dec 27, 2024

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /29

    $319,900

    • 4 Beds
    • 1.5 Baths
    • 1,350 Sq Ft

    115 Boyce Mill Rd, Greensboro, MD 21639

    Welcome to this charming, Cape-Cod with a Full Unfinished basement—perfectly nestled on a spacious 1/2 Acre! This property gives you that “welcome home” feeling the moment you arrive. Inside, you’ll find a bright and inviting living area featuring a cozy electric fireplace insert and beautiful wood‐beam accents. The freshly renovated kitchen is thoughtfully designed and opens seamlessly to the

    Kathleen Brenton Brenton Realty Group

    115 Boyce Mill Rd, Greensboro, MD 21639
  • /29

    $261,000 Sold Jan 13, 2026

    1105 Market St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 2021

    Last Sold Summary

    • $201/SF
    • 85 Days On Market

    Current Estimated Value $264,298

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    1105 Market St, Denton, MD 21629
    • /23

      Est $298,708 Not Listed For Sale

      106 Noble Ave, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1995
      106 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • $243/SF
      • 3 Days On Market
      • Last Sold Price $299,900
      • Jul 26, 2024

      Last Listing Agent Sid Campen Charles C. Powell, Inc. Realtors

  • /13

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    21611 Everlea Dr, Preston, MD 21655

    Welcome to this estate sale opportunity offering convenient one-level living in a wonderful, well-established community just minutes from Easton and St. Michaels. Lovingly owned by the original owner, this 3-bedroom, 2-bath home is ready for its next chapter. The home features a functional floor plan with spacious living areas and offers great potential for updates to match your personal style.

    Nicole Giordano Coldwell Banker Waterman Realty

    21611 Everlea Dr, Preston, MD 21655
  • /19

    $335,000 Sold May 27, 2025

    13061 Logan Ln, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Built 2004

    Last Sold Summary

    • $266/SF
    • 6 Days On Market

    Current Estimated Value $342,281

    Last Listing Agent Megan Carpenter Tesla Realty Group, LLC

    13061 Logan Ln, Greensboro, MD 21639
    • /53

      Est $393,417 Not Listed For Sale

      230 Main St, Preston, MD 21655

      • 5 Beds
      • 5 Baths
      • 3,208 Sq Ft
      • Built 1890
      230 Main St, Preston, MD 21655

      Last Sold Summary

      • 3% Below List Price
      • $126/SF
      • 7 Days On Market
      • Last Sold Price $405,000
      • Nov 06, 2024

      Last Listing Agent Shane Slacum LPT Realty, LLC

  • /31

    $415,000

    • 4 Beds
    • 1.5 Baths
    • 2,885 Sq Ft

    112 S 5th Ave, Denton, MD 21629

    Reduced, sellers are ready to move on! Homes like this is what they use for Christmas cards, large wrap around porch, entry foyer, detailed fireplaces, hard wood floors, and so much more. This is waiting for the right owner to continue the 126 years this home has stood. Everything in this home is in grand size. Large rooms, make this an easy home for a large family . The house current owners have

    Kat Thompson Benson & Mangold, LLC.

    112 S 5th Ave, Denton, MD 21629
  • /48

    $350,000 Sold Jan 14, 2026

    334 Deep Shore Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,640 Sq Ft
    • Built 1957

    Last Sold Summary

    • $213/SF
    • 15 Days On Market

    Current Estimated Value $352,509

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    334 Deep Shore Rd, Denton, MD 21629
    • /17

      Est $284,032 Not Listed For Sale

      104 Noble Ave, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,236 Sq Ft
      • Built 1995
      104 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • 11% Above List Price
      • $206/SF
      • 76 Days On Market
      • Last Sold Price $255,000
      • Feb 13, 2024

      Last Listing Agent Amy Endzel Keller Williams Select Realtors of Annapolis

  • /35

    $379,900

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft

    22403 Marsh Creek Rd, Preston, MD 21655

    Custom Brick rancher, close to town on large lot. Open floor plan, spacious kitchen, stainless steel appliances, large island. 3 bedrooms, 2 baths, sunroom overlooking yard. Upgrades include new windows, CAC, new roof new electric service and plumbing New Septic and Well, Closing help will be considered

    Barbara Nichols Results Realty Inc.

    22403 Marsh Creek Rd, Preston, MD 21655
  • /28

    $233,990 Sold Aug 20, 2025

    124 Julie Ln, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $171/SF
    • 20 Days On Market

    124 Julie Ln, Federalsburg, MD 21632
    • /14

      Est $356,360 Not Listed For Sale

      111 Fooks Ave, Preston, MD 21655

      • 4 Beds
      • 2 Baths
      • 2,072 Sq Ft
      • Built 1974
      111 Fooks Ave, Preston, MD 21655

      Last Sold Summary

      • 6% Above List Price
      • $162/SF
      • 323 Days On Market
      • Last Sold Price $335,000
      • Jul 26, 2024

      Last Listing Agent Barbara Nichols Results Realty Inc.

  • /18

    $340,000

    • 3 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    27279 Jenny Hye Ln, Marydel, MD 21649

    Welcome to Your Peaceful Retreat!This 3-bedroom, 2.5-bath split-foyer home offers 1,488 sq. ft. of comfortable living space, plus a full basement and an attached one-car garage. With its classic brick-and-siding exterior, inviting front patio, and serene surroundings, this property blends warmth, character, and endless potential.Step inside and imagine the possibilities—a bright, open

    Hudson Post Keller Williams Select Realtors of Easton

    27279 Jenny Hye Ln, Marydel, MD 21649
  • /39

    $365,000 Sold Mar 27, 2026

    24029 Meadows Dr, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 1990

    Last Sold Summary

    • $204/SF
    • 67 Days On Market

    Current Estimated Value $389,344

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    24029 Meadows Dr, Ridgely, MD 21660
    • /38

      Est $242,221 Not Listed For Sale

      113 Noble Ave, Preston, MD 21655

      • 2 Beds
      • 1 Bath
      • 1,314 Sq Ft
      • Built 1910
      113 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • 1% Above List Price
      • $183/SF
      • 18 Days On Market
      • Last Sold Price $239,900
      • May 05, 2023

      Last Listing Agent Benjamin Daniels The KW Collective

  • /41

    $399,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    27709 Bright Rd, Goldsboro, MD 21636

    Welcome to 27709 Bright Road in Goldsboro, MD! Just seconds from the Delaware line and only 40 minutes from the Bay Bridge, this wonderful 3 Bedroom, 2 Bathroom Ranch sits on nearly 4 acres of level clearings and beautiful mature woods. If you're looking for incredible value and peace of mind, this is the one! Built rock-solid with 2x6 construction, the home has been so thoughtfully updated that

    Genna Fleming Hyatt & Company Real Estate LLC

    27709 Bright Rd, Goldsboro, MD 21636
  • /20

    $267,490 Sold Aug 12, 2025

    124 Parkland Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $253/SF
    • 6 Days On Market

    D.R. Horton Kinnamon Meadows

    124 Parkland Rd, Greensboro, MD 21639
    • /14

      Est $382,667 Not Listed For Sale

      107 Fooks Ave, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 1,950 Sq Ft
      • Built 2023
      107 Fooks Ave, Preston, MD 21655

      Last Sold Summary

      • 8% Above List Price
      • $181/SF
      • 154 Days On Market
      • Last Sold Price $352,800
      • Feb 16, 2024

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /62

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    1010 S 2nd St, Denton, MD 21629

    Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /2

    $100,000 Sold Feb 20, 2026

    3471 Laurel Grove Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 888 Sq Ft
    • Built 1965

    Last Sold Summary

    • 9% Below List Price
    • $113/SF
    • 31 Days On Market

    Current Estimated Value $142,000

    Last Listing Agent Heather Brummell Keller Williams Realty

    3471 Laurel Grove Rd, Federalsburg, MD 21632
    • /33

      Est $481,636 Not Listed For Sale

      27518 Possum Hill Rd, Federalsburg, MD 21632

      • 4 Beds
      • 3 Baths
      • 2,249 Sq Ft
      • Built 2009
      27518 Possum Hill Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 1% Above List Price
      • $211/SF
      • 173 Days On Market
      • Last Sold Price $474,900
      • Nov 20, 2024

      Last Listing Agent Dustin Parker The Parker Group

  • /22

    $369,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,292 Sq Ft

    3 Sunrise Ave, Ridgely, MD 21660

    ***New Construction - Under Construction now with estimated completion of April 2026. Photos are of model previously built.*** This modern "Farmhouse" Rancher is thoughtfully designed and constructed by the reputable Lomaxx Custom Homes, offering the perfect combination of style, functionality, and comfort. This beautiful home features 3 bedrooms, 2 full bathrooms, and an inviting open-concept

    Amy Betts Coldwell Banker Realty

    3 Sunrise Ave, Ridgely, MD 21660
  • /11

    $1,050,000 Sold May 16, 2025

    5890 Harmony Rd, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 2,264 Sq Ft
    • Built 1920

    Last Sold Summary

    • $464/SF
    • 6 Days On Market

    Current Estimated Value $1,071,417

    Last Listing Agent Nick Campanaro The Land Group

    5890 Harmony Rd, Preston, MD 21655
    • /37

      Est $381,994 Not Listed For Sale

      1103 Trice Meadows Cir, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,816 Sq Ft
      • Built 2010
      1103 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 6% Above List Price
      • $128/SF
      • 3 Days On Market
      • Last Sold Price $360,000
      • Oct 26, 2023

      Last Listing Agent Crystal Smith RE/MAX

  • /15

    $135,000

    • 3 Beds
    • 1.5 Baths
    • 1,664 Sq Ft

    501 Lincoln St, Denton, MD 21629

    Property is being sold As/ Is. Located on a corner lot. Owner has completed some work to the property, but additional work will be required. Please contact Denton Planning and Codes to verify remaining requirements to obtain an occupancy permit.

    Diane Wenk Wright Real Estate

    501 Lincoln St, Denton, MD 21629
  • /26

    $269,000 Sold Apr 23, 2026

    311 Holt St, Federalsburg, MD 21632

    • 3 Beds
    • 1.5 Baths
    • 1,696 Sq Ft
    • Built 1895

    Last Sold Summary

    • $159/SF
    • 5 Days On Market

    Current Estimated Value $235,876

    Last Listing Agent Heather Brummell Keller Williams Realty

    311 Holt St, Federalsburg, MD 21632
    • /19

      Est $351,609 Not Listed For Sale

      344 Meadow Vale Ln, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,580 Sq Ft
      • Built 2010
      344 Meadow Vale Ln, Denton, MD 21629

      Last Sold Summary

      • 4% Above List Price
      • $215/SF
      • 52 Days On Market
      • Last Sold Price $339,000
      • Jun 17, 2024

      Last Listing Agent Bonnie Johnson Keller Williams Realty

  • /5

    $305,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3390 Jefferson Pond Rd, Federalsburg, MD 21632

    Beautiful new construction in a charming, up-and-coming community! This 3-bedroom, 2-bath home features an open-concept layout with luxury vinyl plank flooring throughout the main living areas. The spacious kitchen offers granite countertops, modern finishes, and seamless flow into the living and dining spaces—perfect for entertaining. Built for peace of mind with 30-year architectural shingles

    Amy Herr Keller Williams Realty

    3390 Jefferson Pond Rd, Federalsburg, MD 21632
  • /10

    $125,000 Sold Jan 15, 2026

    311 Maple Ave, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 1,230 Sq Ft
    • Built 1940

    Last Sold Summary

    • 7% Below List Price
    • $102/SF
    • 4 Days On Market

    Current Estimated Value $126,939

    Last Listing Agent Melissa Tippett TTR Sotheby's International Realty

    311 Maple Ave, Federalsburg, MD 21632
    • /13

      Est $274,533 Not Listed For Sale

      12185 River Rd, Ridgely, MD 21660

      • 2 Beds
      • 1 Bath
      • 1,026 Sq Ft
      • Built 1990
      12185 River Rd, Ridgely, MD 21660

      Last Sold Summary

      • 6% Above List Price
      • $253/SF
      • 5 Days On Market
      • Last Sold Price $260,000
      • Jun 21, 2024

      Last Listing Agent Kelly Dahle Benson & Mangold, LLC

  • /34

    $210,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    27320 Chipmans Ln, Federalsburg, MD 21632

    SELLERS ARE MOTIVATED Charming country rancher with peaceful farmland views! Welcome to 27320 Chipmans Lane in Federalsburg, MD—this quaint 3-bedroom, 1-bath home offers a great blend of comfort, updates, and rural tranquility. Situated on over 1/3 of an acre, this home features a beautifully updated bathroom, a newer roof (just a few years old), and a brand new well—providing peace of mind for

    Justin Pokrywka Taylor Properties

    27320 Chipmans Ln, Federalsburg, MD 21632
  • /29

    $275,000 Sold Oct 21, 2025

    104 Roe St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 1948

    Last Sold Summary

    • $228/SF
    • 3 Days On Market

    Current Estimated Value $262,732

    Last Listing Agent Nora Turner Long & Foster Real Estate, Inc.

    104 Roe St, Greensboro, MD 21639
    • /12

      Est $1,454,836 Not Listed For Sale

      12786 Holly Rd, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,728 Sq Ft
      • Built 1870
      12786 Holly Rd, Greensboro, MD 21639

      Last Sold Summary

      • 23% Below List Price
      • $1,100/SF
      • 60 Days On Market
      • Last Sold Price $1,900,000
      • Dec 11, 2024

      Last Listing Agent Benjamin Alder The Land Group

  • /25

    $254,900

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft

    28241 Hickman Cannery Rd, Denton, MD 21629

    Welcome to 28241 Hickman Cannery Road, a refreshed two-story home in Denton, MD, blending classic charm with modern, low-maintenance updates. Luxury vinyl plank flooring runs throughout both levels, creating a cohesive, move-in-ready feel. The main level offers a bright living room, a flexible den ideal for a home office or family room, a spacious kitchen, dedicated laundry room, and a full

    Billy Mister Keller Williams Realty

    28241 Hickman Cannery Rd, Denton, MD 21629
  • /26

    $185,000 Sold Nov 10, 2025

    311 Reliance Ave, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 1,224 Sq Ft
    • Built 1950

    Last Sold Summary

    • $151/SF
    • 7 Days On Market

    Current Estimated Value $187,529

    Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    311 Reliance Ave, Federalsburg, MD 21632
    • /36

      Est $725,404 Not Listed For Sale

      24638 Tribbett Cir, Ridgely, MD 21660

      • 5 Beds
      • 3 Baths
      • 4,521 Sq Ft
      • Built 2010
      24638 Tribbett Cir, Ridgely, MD 21660

      Last Sold Summary

      • 16% Above List Price
      • $138/SF
      • 19 Days On Market
      • Last Sold Price $625,000
      • May 12, 2023

      Last Listing Agent John Currence BHHS PenFed (actual)

  • /38

    $99,000

    • Land
    • 9,147 Sq Ft
    • $471,429 per Acre

    504 Central Ave, Ridgely, MD 21660

    UPDATE: The New Ridgely Comprehensive Plan draft will designate this lot for future commercial growth alongside the adjoining property—making this a strong investment opportunity. Call to request the documentation. This .21-acre vacant lot is ideally located in the heart of Ridgely. Currently zoned residential, yet future commercial allowance almost finalized - it offers access to public water

    Allie Harris Taylor Properties

    504 Central Ave, Ridgely, MD 21660
  • /27

    $219,990 Sold Aug 14, 2025

    157 Riverwalk Terrace, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $161/SF
    • 14 Days On Market

    Current Estimated Value $201,000

    157 Riverwalk Terrace, Federalsburg, MD 21632

Showing Results 121 - 160, Page 4 of 18

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